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Evidence for heterolytic cleavage of a cyclic oxonium ylide: implications for the mechanism of the Stevens [1,2]-shift

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Abstract

Formation and rearrangement of several oxonium ylides containing cyclopropylcarbinyl migrating groups were studied. Efficient ring-contraction by [1,2]-shift to form cyclopropane-substituted cyclobutanones was observed, with no competing cyclopropane fragmentation. Substitution with the hypersensitive mechanistic probe (trans,trans-2-methoxy-3-phenylcyclopropyl)methyl led to cyclopropane fragmentation via an apparent heterolytic pathway, providing the first evidence for ion pair intermediates from ylide cleavage, and suggesting a possible alternative heterolytic mechanism for the Stevens [1,2]-shift.

Graphical abstract: Evidence for heterolytic cleavage of a cyclic oxonium ylide: implications for the mechanism of the Stevens [1,2]-shift

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Publication details

The article was received on 04 Oct 2017, accepted on 06 Nov 2017 and first published on 07 Nov 2017


Article type: Communication
DOI: 10.1039/C7CC07716E
Citation: Chem. Commun., 2017, Advance Article
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    Evidence for heterolytic cleavage of a cyclic oxonium ylide: implications for the mechanism of the Stevens [1,2]-shift

    S. N. Hosseini, J. R. Johnston and F. G. West, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC07716E

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